Synthesis of substituted imidazoles via organocatalysis

被引：172

作者：

Frantz, DE

Morency, L

Soheili, A

Murry, JA

Grabowski, EJJ

Tillyer, RD

机构：

[1] Merck & Co Inc, Merck Res Labs, Dept Proc Res, Wayne, PA 19087 USA

[2] Merck & Co Inc, Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 05期

关键词：

D O I：

10.1021/ol0498803

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot synthesis of substituted imidazoles is described. The cornerstone of this methodology involves the thiazolium-catalyzed addition of an aldehyde to an acyl Imine to generate the corresponding alpha-ketoamide in situ followed by ring closure to the imidazole in a one-pot sequence. The extension of this methodology to the one-pot synthesis of substituted oxazoles and thiazoles is also described.

引用

页码：843 / 846

页数：4

共 46 条

[41] BASE-INDUCED CYCLOADDITION OF SULFONYLMETHYL ISOCYANIDES TO C,N DOUBLE-BONDS - SYNTHESIS OF 1,5-DISUBSTITUTED AND 1,4,5-TRISUBSTITUTED IMIDAZOLES FROM ALDIMINES AND IMIDOYL CHLORIDES
VANLEUSEN, AM
WILDEMAN, J
OLDENZIEL, OH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (07) : 1153 - 1159
[42] Identification of regioisomers in a series of N-substituted pyridin-4-yl imidazole derivatives by regiospecific synthesis, GC/MS, and 1H NMR
Wagner, GK
Kotschenreuther, D
Zimmermann, W
Laufer, SA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) : 4527 - 4530
[43] A NEW SYNTHESIS OF HIGHLY FUNCTIONALIZED OXAZOLES
WIPF, P
MILLER, CP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) : 3604 - 3606
[44] Total synthesis of dendroamide A: Oxazole and thiazole construction using an oxodiphosphonium salt
You, SL
Kelly, JW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) : 9506 - 9509
[45] Addition of azoles and amines to unsymmetrical fumaric esters
Zaderenko, P
Lopez, MC
Ballesteros, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) : 6825 - 6828
[46] RESOLUTION OF 2-AZO-1-YLSUCCINIC ESTERS BY ENANTIOSELECTIVE INCLUSION METHODOLOGY
ZADERENKO, P
LOPEZ, P
BALLESTEROS, P
TAKUMI, H
TODA, F
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (02) : 381 - 384

← 1 2 3 4 5 →